Hypoglycemic N,N-arylsulfonylglycine compounds

Abstract

A compound of formula l: wherein, R 1 , R 2 and R 3 independently represent hydrogen, alkyl, alkenyl, alkynyl, aryl, or aralkyl groups having 1 to 8 carbon atoms; X represents an alkoxyalkyl, alkoxyaryl, alkoxyalkylaryl, aralkylalkoxy, or alkoxyalkylheterocycle; or a pharmaceutically acceptable salt or prodrug thereof.

What is claimed is:  
     
       1. A compound of formula I:                    
       wherein, 
       R 1 , R 2 , and R 3  independently represent hydrogen, alkyl, alkenyl, alkynyl, aryl, or aralkyl groups having 1 to 8 carbon atoms;  
       X represents an alkoxyalkyl, alkoxyaryl, alkoxyalkylaryl, aralkylalkoxy, or alkoxyalkylheterocycle; or a pharmaceutically acceptable salt or prodrug thereof.  
     
     
       2. The compound according to  claim 1  depicted by formula II:                    
       wherein the X of formula (I) is OR 4 , and R 4  is a group selected from aryl, aralkyl, alkyaryl, alkylheterocyclic, or alkylarylheterocyclic; or a pharmaceutically acceptable salt thereof. 
     
     
       3. The compound according to  claim 1  wherein X is the group 2-Phenyl-4-oxazolylethoxy, R 1  and R 2  are hydrogen and R 3  is selected from the group consisting of alkyl, aryl, aralkyl, and alkylaryl. 
     
     
       4. A compound selected from the group consisting of: 
       N-[4-(2-(Phenyloxazol-4yl)ethoxy)phenyl]-N-isopropyl sulfonylglycine represented by the formula:                    
       N-4[-(2-(Phenyloxazol-4yl)ethoxy)phenyl]-N-methylsufonyl-glycine represented by the formula:                    
       N-[4-(2-(Phenyloxazol-4yl)ethoxy)phenyl]-N-N′N′-dimethyl aminosulfonylglycine represented by the formula:                    
       N-[4-(2-(Phenyloxazol-4yl)ethoxy)phenyl]-N-phenylmethyl sulfonylglycine represented by the formula:                    
       and, 
       N-[5-(2-(2-Naphthylmethyl)benzofuranyl)]-N-methylsufonyl glycine                    
       or a pharmaceutically acceptable salt or prodrug thereof. 
     
     
       5. A pharmaceutical formulation comprising as an active ingredient the compound of formula (I), as claimed in any one of  claims 1  to  3 , together with one or more pharmaceutically acceptable excipients. 
     
     
       6. A method of treating hyperglycemia in a mammal in need thereof comprising administering to a mammal in need thereof an effective amount of the compound of  claim 1 . 
     
     
       7. A method of treating hyperlipidemia in a mammal in need thereof comprising administering to said mammal an effective amount of the compound of  claim 1 . 
     
     
       8. A method of treating hyperglycemia comprising administering to a mammal in need thereof an effective amount of the compound of  claim 3 . 
     
     
       9. A method of treating hyperlipidemia comprising administering to a mammal in need thereof an effective amount of the compound of  claim 3 .